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Record Information
Version	2.0
Creation Date	2012-05-31 14:08:37 -0600
Update Date	2015-06-03 15:54:52 -0600
Secondary Accession Numbers	ECMDB06488
Identification
Name:	N-Acetyl-L-glutamate 5-semialdehyde
Description	N-Acetyl-L-glutamate 5-semialdehyde is an intermediate in Urea cycle and metabolism of amino groups. N-Acetyl-L-glutamate 5-semialdehyde is the
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb0d0f934> Close
Synonyms:	2-Acetamido-5-oxopentanoate 2-Acetamido-5-oxopentanoic acid N-acetyl-L-glutamate semialdehyde N-acetyl-L-glutamate-5-semialdehyde N-acetylglutamate γ-semialdehyde N-acetylglutamate semialdehyde N-Acetyl-L-glutamate semialdehyde N-Acetyl-L-glutamate-5-semialdehyde N-Acetyl-L-glutamic acid 5-semialdehyde N-Acetyl-L-glutamic acid semialdehyde n-Acetyl-L-glutamic acid-5-semialdehyde N-Acetyl-L-glutamic acid-5-semialdehyde n-Acetylglutamate γ-semialdehyde N-Acetylglutamate g-semialdehyde N-Acetylglutamate gamma-semialdehyde N-Acetylglutamate semialdehyde N-Acetylglutamate γ-semialdehyde n-Acetylglutamic acid γ-semialdehyde N-Acetylglutamic acid g-semialdehyde N-Acetylglutamic acid gamma-semialdehyde N-Acetylglutamic acid semialdehyde N-Acetylglutamic acid γ-semialdehyde N-AcGlu-semialdehyde
Chemical Formula:	C7H11NO4
Weight:	Average: 173.1665 Monoisotopic: 173.068807845
InChI Key:	BCPSFKBPHHBDAI-LURJTMIESA-N
InChI:	InChI=1S/C7H11NO4/c1-5(10)8-6(7(11)12)3-2-4-9/h4,6H,2-3H2,1H3,(H,8,10)(H,11,12)/t6-/m0/s1
CAS number:	13074-21-0
IUPAC Name:	(2S)-2-acetamido-5-oxopentanoic acid
Traditional IUPAC Name:	N-acetyl-5-oxo-L-norvaline
SMILES:	CC(=O)N[C@@H](CCC=O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	N-acyl-L-alpha-amino acids
Alternative Parents	Fatty acids and conjugates Alpha-hydrogen aldehydes Acetamides Secondary carboxylic acid amides Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
Substituents	N-acyl-l-alpha-amino acid Fatty acid Alpha-hydrogen aldehyde Acetamide Carboxamide group Secondary carboxylic acid amide Monocarboxylic acid or derivatives Carboxylic acid Organopnictogen compound Organic oxygen compound Organooxygen compound Organonitrogen compound Aldehyde Carbonyl group Organic nitrogen compound Organic oxide Hydrocarbon derivative Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	acetamides (CHEBI:16319 ) glutamic semialdehyde (CHEBI:16319 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 18.6 g/L ALOGPS logP -0.43 ALOGPS logP -1.3 ChemAxon logS -0.97 ALOGPS pKa (Strongest Acidic) 3.72 ChemAxon pKa (Strongest Basic) -1.8 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 83.47 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 39.81 m³·mol⁻¹ ChemAxon Polarizability 16.46 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate N-Acetyl-L-glutamate 5-semialdehyde + Water > Acetic acid + L-Glutamic-gamma-semialdehyde N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH N-Acetylornithine + Oxoglutaric acid < N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate N-Acetyl-L-glutamate 5-semialdehyde + NADP + Inorganic phosphate > N-Acetyl-L-glutamyl 5-phosphate + NADPH N-Acetylornithine + Oxoglutaric acid > N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + N-Acetylornithine N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
SMPDB Pathways:	Lysine biosynthesis PW000771 arginine metabolism PW000790 ornithine metabolism PW000791
KEGG Pathways:	Arginine and proline metabolism ec00330 Lysine biosynthesis ec00300 Metabolic pathways eco01100
EcoCyc Pathways:	ornithine biosynthesis GLUTORN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-054o-9500000000-209b524fd8ef1d9e627f View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-006x-9420000000-8d264158e366f88d5d3e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-05fr-1900000000-cfaeff3cecd86134fd58 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-055r-6900000000-bb54f50a29e9a351858c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-02a6-9100000000-fe9c1618b7f81c2f9d5b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00di-0900000000-f6338ed4d753ef0b744e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0m89-3900000000-b5fbc1c314380afa8cc1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-052f-9100000000-a529029ad524b613c990 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01q9-0900000000-1f0440fa922d5815c5d9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03e9-5900000000-b295f71616c68600654d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-0d07a69d508963a4c246 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-2900000000-d1bb675eb0f08dff7304 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01q9-3900000000-a872856bc77482a41b25 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-052f-9000000000-76a9b5ce42ea1d2112d2 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16319 HMDB ID HMDB06488 Pubchem Compound ID 192878 Kegg ID C01250 ChemSpider ID 167387 Wikipedia ID Not Available BioCyc ID CPD-469 EcoCyc ID CPD-469

Enzymes